Method for preparing dianhydrohexitol diester compositions

A kind of technology of two anhydro hexitol and composition, applied in the properties of diester and/or colorant, two anhydro hexitol, the application field of the aforementioned composition in various industrial fields, can solve the complex method and Expensive and other issues, to achieve the effect of improving the color

Active Publication Date: 2008-04-02
ROQUETTE FRERES SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0039] The process is more complex and expensive because the macroporous resin used with the activated carbon during esterification cannot be effectively re-used when it is contaminated by the activated carbon and the colorants adsorbed by it

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] One test (Test 1) according to the invention was carried out according to the following general procedure.

[0145] 146 g of isosorbide (1 mol) and 432 g of n-octanoic acid (3 mol) were charged into a 1 liter glass reactor equipped with jacket, helical stirrer, thermometer, distillation head combined with condenser and distillation collector, clamp The jacket is heated by a thermostat bath with circulating oil.

[0146] The stirring system was operated at a speed of 400 rpm and the thermostat bath was set to 100°C. When the temperature of the reaction medium reaches 60°C, add as follows: 2.92 g of p-toluenesulfonic acid (PTSA) monohydrate (its dry weight is 1.8% relative to the dry weight of isosorbide) and 0.90 g of 50% hypophosphorous acid, i.e. its dry weight 0.3% by weight relative to the dry weight of isosorbide and a ratio of about 0.15 / 1 relative to PTSA.

[0147] The thermostat bath was then set to a constant 150° C. and stirred at a speed of 650 rpm. All compo...

Embodiment 2

[0159] Other tests according to the present invention (TESTS 2-7 below) are carried out according to the general process described in Test 1, except that the following changes are introduced:

[0160] TEST 2: The esterification reaction continued for 6 hours instead of 5 hours;

[0161] TEST 3: Replace 1.8% PTSA with dry weight 1.1% methanesulfonic acid;

[0162] TEST 4: Replace 1.8% of PTSA by dry weight with "Amberlyst 15 (dry)" type porous value of 11% by dry weight;

[0163] TEST 5: 1.9% dry weight phosphotungstic acid was used instead of 1.8% dry weight PTSA, and the esterification reaction was carried out under nitrogen injection or under vacuum;

[0164] TEST 6: n-octanoic acid was replaced by 2-ethylhexanoic acid (mol / mol), and the esterification reaction was continued for 7.5 hours at 160-175°C and 100mbar vacuum; and

[0165] TEST 7: Isosorbide was replaced by isoidide, and the esterification reaction was completed in 3.5 hours instead of 5 hours.

[0166] The fol...

Embodiment 3

[0181] In this example, tests not in accordance with the invention (TESTS C2-25) were carried out in the same manner as TEST C1 according to Example 1, except that the following changes were introduced:

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Abstract

The invention concerns a method for preparing a dianhydrohexitol diester composition, characterized in that it comprises a step which consists in esterifying a dianhydrohexitol composition with a carboxylic acid in the presence of an acid catalyst and hypophosphorous acid. Preferably, the hypophosphorous acid is introduced in an amount ranging between 0.05 and 2 wt. % of dianhydrohexitol, and in a hypophosphorous acid / acid catalyst weight ratio less than 1 / 1. Said method enables novel dianhydrohexitol diester compositions, for example isosorbide diesters, isomannide and / or isoidide richer in diester(s) and / or less coloured, useful in numerous industrial applications, in particular in plastic compositions, to be obtained.

Description

technical field [0001] The subject of the present invention relates to the preparation of diester compositions of dianhydrohexitols such as isosorbide, isoidide, isomannide or isogalactide new preparation method. [0002] The invention also relates to the properties of these compositions as new industrial products, especially selected for diesters and / or colorants. [0003] Finally it also relates to the use of the aforementioned composition in various industrial fields, especially in the field of plastics. Background technique [0004] The preparation of esters of anhydrohexitols has been known for over 60 years and is described inter alia in the following patents published in the 1940's by a company named Atlas Powder Company: [0005] US2322820 relates to the preparation of anhydrohexitol (sorbitol, mannitol) and / or hexoside (sorboside=isosorbide or mannoside=isomannitol) monoester compositions; [0006] US2322821 relates to the preparation of compositions of isosorbid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 帕特里克·富埃尔特斯埃尔韦·维亚尔
Owner ROQUETTE FRERES SA
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